Imidazolium quaternary salts and methods of preparing same



United States Patent 3,042,675 IMIDAZOLIUM QUATERNARY SALTS AND METHODSOF PREPARING SAME Edward F. Rogers, Middletown, and Robert L. Clark,

Woodbridge, N.J., assignors to Merck & Co., Inc., Rahway, NJ., acorporation of New Jersey No Drawing. Filed Feb. 2, 1960, Ser. No. 6,104

14 Claims. (Cl. 260256.4)

This invention relates to novel imidazolium quaternary salts. Moreparticularly, it relates to 3-(2-substituted-4- amino 5pyrimidylmethyl)-1-substituted imidazo-lium quaternary salts and methodsof preparing the same. It is also concerned with compositions containingsuch salts.

According to the present invention there are provided novel 3 (2perfluoroloweralkyl-4-amino-5-pyrimidylmethyD-l-substituted imidazoliumand 3-[2-(3,3,3-trifiuoropropyl)4-amino-5-pyrimidylmethyl]-l-substituted imidazolium quaternary saltswherein the imidazole ring is substituted 'at the 1-position by an allylor lower alkyl radical. These quaternary salts have useful medicinalproperties and are particularly suitable for use in the treatment andprevention of coccidiosis in poultry.

The 3 (2 perfluoroloweralkyl-4-amino-5-pyrimidylmethyl) -1-allylimidazolium and 3-(2-perfiuoroloweralkyl- 4amino-5-pyrimidylmethyl)-1-lower alkylated imidazolium quaternary saltsof the present invention may be represented by the structural formula NRV 1 NH: b (A) wherein R is a perfluoroloweralkyl radical, R is selectedfrom the group consisting of allyl and lower alkyl, X is an anion, and bis a positive number having a value such that the negative charge of theanion X is neutralized by 1) moles of cation. Thus, fr'or example, whenX is a monoyalent anion such as a halide, b is 1.

Similarly, the 3-[2-(3,3,3-trifluoropropyl)-4-amino-5-pyrimidylmethyH-l-allyl imidazolium and 3-[2-(3,3,3- trifluoropropyl) 4arnino-S-pyrirnidylmethyll-1-lower 'alkyla ted imidazolium quaternarysalts with which this invention is also concerned may be represented bythe formula N CFaCHzGH 1} N3 i NH3+ V, b (B) wherein R and X are aspreviously defined, and b and c are positive numbers having values suchthat b moles of cation is neutralized by moles of anion X. Thus, for

example, in formula B above when X is a monovalent anion such as ahalide, b is 1 and c is 2.

As will be apparent from the above structural formulae, the compoundsdescribed herein may be considered as substituted imidazoles. Theimidazole ring is substituted at the 3-position by a2-perfluoroloweralkyl-4-amino-5- pyrimidylmethyl or2-(3,3,3-trifiuoropropyl)-4-amino5- pyrimidylmethyl radical. It isfurther substituted at the 1-position by an allyl or lower alkylradical. The pyrimidine moiety contains at the 2- positon of thepyrimidine ring a 3,3,3-trifiuoropropyl or perfluoroloweralltyl radicalsuch as perfluoromethyl, perfiuoroethyl, perfluoropropyl,perfluoroisopropyl, perfluorobutyl and the like.

With iurther' regard to Formulas A and B, the anion (designated as X)may be an inorganic anion such as chloride, bromide, iodide, nitrate,sulfate, phosphate and 2 the like, or the anion of an organic acid suchas citric, tartaric, acetic, picric, stearic, succinic, benzoic,phthalic, phenoxyacetic, embonic, abietic, 2-naphthalenesulfonic orethylenediamine tetraacetic acids. It may also be the anion of a polymersuch as polyphosphate or polystyrenesulfonate ion. The nature of theanion is not critical and any anion may be employed as long as it is notunduly toxic for poultry. However, the anions of the mineral acids andstrong organic acids are preferred. It will be readily realized by thoseskilled in this art that an acid addition salt of the primary aminogroup present in the compounds represented by formula B above, namelythe 3 [2.-(3,3,3-trifiuoropropyl)-4-amino-S-pyrimidylmethyfll-allylimidazolium and 3-[2-(3,3,3-trifiuoropropyl) 4-amino-S-pyrimidylmethyl]-1-lower alkylated imidazolium quaternary salts,will also be formed concurrently with the quaternary salt. Accordingly,it is to be understood that when the expression salt is used in thisspecification and appended claims to define the quaternary saltsrepresen-ted by Formula B, such expression is being employed todesignate the acid addition salt of such quaternary salts. l 1 I i j Thecompounds of this invention are prepared by re acting together anappropriately substituted pyrimidine and a 1-( allyl or lower alkyl)imidazole. As the pyrimidine reactant we may employ an acid additionsalt of an ester of a 2- (perfiuoroloweralkyl or 3,3,3-t1ifluoropropyl)-4-amino-5-hydroxymethyl pyrimidine and a strong acid such as ahydrohalic acid. According to the preferred process, a'2-perfluoroloweralkyl-4-arnino-S halomethyI pyrimidine hydrohalide or2-(3,3,3-trifiuoropropyl)-4- amino-S-halomethyl pyrimidine dihydrohalideis reacted directly with the substituted imidazole. This process may berepresented as follows:

where R is a perfiuoroloweralkyl radical, R is an allyl or lower alkylradical and X is a halogen such as chlorine or bromine.

Although the proportions of reactants are indicated to be equimolar inthe above equations suchproportions are not critical and an excess ofeither reactant can also be suitably reacted. Preferably, however, anexcess of the substituted imidazole reactant is employed.

The reaction is preferably carried out in the presence of an organicsolvent which is inert under the reaction conditions. Illustrative ofthe solvents which may be employed as the reaction medium are the loweralkanols, such as methanol, ethanol, propanol and the likeiaceto V 3 (2perfluoroethyl 4 amino nitrile and the N,N-diloweralkyl alkanoamides.The reaction temperature is not critical and it is preferred to carryout the process at about room temperature. At room temperature thereaction is generally complete after from -20 hours or more according tothe concentration of reactants and particular reactants employed.However, appreciable amounts of the product are obtained after a shortperiod of time. The products precipitate out from the reaction mixtureon standing at room temperature or on the addition of a suitableprecipitant such as ether, ethyl acetate and the like and can berecovered by filtration or other conventional techniques.

Although the acid addition salt of the S-hydroxymethyl pyrimidine estersof hydrohalic acids, i.e. the halomethyl pyrimidine hydrohalides ordihydrohalides, are preferably employed for'reaction with thesubstituted imidazoles, the acid addition salt of the S-hydroxymethylpyrimidine esters of other strong inorganic acids such as nitric,phosphoric, sulfuric and the like may be used. In addition, thequaternization may also be brought about employing the acid additionsalt of the 5-hydroxymethyl pyrimidine esters of strong organic acidssuch as the methyl sulfonate, p-toluenesulfonate, benzenesulfonate andnaphthalenesulfonate esters.

The quaternization may be conducted so that the particular salt desiredis obtained directly or the quaternary salt recovered from the reactionmedium may be 'conveniently metathesized to the desired salt bytechniques known in the art.

Among the3-(2-perfluoroloweralkyl-4-amino-5-pyrimidyhnethyD-l-substitutedimidazolium and 3-[2-(3,3,3- trifluoropropyl) 4 amino 5 pyrimidylmethyl]1- substituted imidazolium quaternary salts which may be formedaccording to the present invention are the 3-(2-perfluoromethyl 4 amino5 pyrimidylmethyl)- l-methyl imidazolium salts,

3 (2 perfluoromethyl 4 amino 5 pyrirnidylmethyl) -1-ethyl imidazolium'salts,

3 (2 perfluoroethyl 4 amino 5 pyrimidylmethyl)- l-methyl imidazoliumsalts, V

3 (2 perfluoroethyl 4 amino 5 pyrimidylmethyl)- l-ethyl imidazoliumsalts,

I 5 pyrimidylmethyD- l-allyl imidazolium salts,

3 (2 -perfluoro n propyl 4 amino 5 pyrimidylmethyD-l-ethyljmidazoliumsalts, 1

3 (2 r perfiuoro n butyl 4 amino 5 pyrimidylmethyD-l-ethyl imidazoliumsalts,

3 [2 (3,3,3 trifluoropropyl) 4 amino 5 pyrimidylmethyH-l-methylimidazolium salts and 3 [2 (3,3,3 trifluoropropyl) 4 amino 5-pyrimidylmethyl1-l-allyl imidazolium salts.

As previously indicated herein, the compounds of this invention areuseful in the treatment and prevention of coccidiosis in poultry. Thesecompounds are conveniently fed topoultry as a component of the feed ofthe animals although they may also be given dissolved or suspended inthe drinking water. According to one aspect of the invention, novelcompositions are provided in which an imidazolium quaternary salt ispresent as an active anticoccidial ingredient.' Such compositionscomprise the.

quaternary salts intimately dispersed in or admixed with an 1nertcarrier or diluent. 'By an inert carrier is meant one that isnon-reactive with respect to the quaternary and-thatmay :be administeredwith safety to the animals.

Th e carrieror diluent is preferably one that is or may bean ingredientof the animal feed. I The compositions which are a preferred feature ofthe invention are-the so-called feed supplements in which the activeingredient is present in relatviely large amounts and which aresuitable-for additionto the poultry feed directly or after anintermediate dilution or blending step. Euramplesof carriers or diluentssuitable for such compositions are solid orally ingestablej carrierssuch as distillers dried grains, corn meal, citrus meal, fermentationresidues, ground oyster shells, Attapulgus clay, wheat shorts, molassessolubles, corn cob meal, edible vegetable substances, toasted dehulledsoya flour, soybean rnill feed, antibiotic mycelia, soya grits, crushedlimestone and the like. The quaternary salts are intimately dispersed oradmixed throughout the solid inert carrier by methods such as grinding,stirring, milling or tumbling. By selecting proper diluents and byaltering the ratio of carrier to active ingredient, compositions of anydesired concentration may be prepared. Formulations containing fromabout 1% to about 40% by Weight, and preferably from about 225% byweight of active ingredient are particularly suitable for addition topoultry feeds, and compositions containing'from. about 5.l5% by weightof coccidiostat are very satisfactory. The active. compound is normallydispersed or mixed uniformly in the diluent but in some instances may besorbed on the carrier. The optimal concentration of coccidiostat inthese feed supplements will depend to some extent on the particularcompoundjemployed. Since it is convenient for the feed manufacturer touse about onepound of feed supplement for each ton of finished feed, thepreferred concentration of any one of our coccidiostats in a feedsupplement is partly a function of the level of active ingredientdesired in the finished feed.

Examples of typical feed supplements containing a imidazolium quaternarysalt dispersed in -a solid inert carrier are:

B. 3-(2-perfluoroethy1-4-amino-5-pyrimidylmethyl)- l-methyl imidazoliumbromide 10.0 Corn distillers dried grains 90.0

C. 3 (2-perfluoromethyl-4-amino-5-pyrimidylmethyl)-1-ethyl imidazoliumchloride 15.0 Wheat standard middlings; 85.0

D. 3 (2-perfluoroethyl-4-amino-5-pyrimidylmeth yD-I-ethyl imidazoliumchloride 20.0 Corn germ meal; 30.0 Corn distillers grains 50.0

E. 3 (2-perfiuoroethyl-4-amino-5-pyrimidylmethyl)-1allyl imidazoliumchloride 5.0 Fermentation residues 50.0 Wheat shorts 45.0

F. Di[3 (2-perfluoro-n-propyl-4-amino-S-pyrimid- -ylmethyl)-l-ethylimidazolium] sulfate 12.0 Molasses solubles 88.0

G. Di[3 (2-perfluoro-n-butyl-4-amino-5 pyrimidyltmethyD-l-ethylimidazolium] embonate 40.0 Ground oyster shells 60.0

. H. 3-[2-(3,3,3-trifluoropropyl)-4-amino-5-pyrimidylmethyl1-1-methylimidazolium chloride hydrochloride 20.0 Corn germ meal 30o Corndistillers grains 50.0

These and similar 'feed supplements are prepared by uniformly mixing theimidazolium quaternary salt with the carrier or carriers.

The feed supplements of the type illustrated hereinabove are usuallyfurther diluted with materials such as this invention are eflective whenadministered in concentrations of about 0.005% to 0.05% in the diet. Formost satisfactory results from the standpoint of both efficacy andincidence of undesirable side efiects it is preferred that the poultryfeed contain between about 0.0025% and 0.025% by weight of imidazoliumsalt. When the imidazolium salts are to be employed as therapeuticagents, the higher concentrations may be used for relatively shortperiods of time. Thus, concentrations of about 0.02% to 0.05% by weightof the feed may be advantageously administered in treating anestablished outbreak of coccidiosis. When these compounds are employedas therapeutic agents it is desirable to employ the lowest levels thatafford fully adequate control of coccidiosis in order to eliminate asfar as possible any risk of side effects that might appear on prolongedfeeding of the compounds.

Many of the imidazolium quaternary salts of this invention are desirablyor advantageously administered to poultry by way of the drinking waterof the birds. This method of treatment is often employed in thetherapeutic use of our compounds since poultry with coccidiosis are aptto consume less solid feed than normal birds. The water-solublequaternary salts may be added directly to the drinking water.Alternatively, water-soluble powders may be prepared, in which thecoccidiostat is intimately admixed with a suitable carrier, such asdextrose or sucrose, and these powders added to the drinking Water ofpoultry as necessary. Such water-soluble powders may contain any desiredconcentration of coccidiostat and preparations containing from 125%' byweight of active compound are suitable.

The following examples are added to illustrate the production ofspecific compounds provided by this invention but it is understood thatthe invention is not to be restricted thereby to the embodimentsdisclosed in these examples.

EXAMPLE 1 EXAMPLE 2 3-(Z-Perfluoromethy[-4-Amin0-5-Pyrimidylmethyl)-J-Methyl Imidazolium Bromide To 5.0 g. of2-perfiuoromethyl-4-amino-5-pyrimidylmethyl bromide hydrobromidesuspended in m1. of acetonitrile is added 3.7 g. of l-methyl imidazole.After allowing the mixture to stand overnight at room tem-' perature thesolid 3-(2-perfluoromethyl-4-amino-5-pyrimidylmethyl) 1 methylimidazolium bromide which forms is recovered by filtration, washed withacetone and dried to constant weight.

EXAMPLE 3 3 (2-Perflu0r0ethyl-4-Amino-5 -Pyrimidylmethyl 1 -A llylImidazolium Bromide The procedure of Example 2 is followed and 15.5 g.of 2-perfluoroethyl-4-amino-5-pyrimidylmethyl bromide hydrobromidesuspended in 75 ml. of methanol is reacted with 13.0 g. of l-allylimidazole to produce the 3-(2- perfiuoroethyl4-arnino-5-pyrimidylmethyl) -1-allyl imidazolium bromide.

6 EXAMPLE .4

3-(2-Perfluoro-n-Propyl-4-Amino-S-PyrimidylmethyD- I-Ethyl ImidazoliumChloride To a suspension of 7.0 .g. of 2-perfluoro-n-propyl-4-amino-S-pyrimidylmethyl chloride hydrochloride in ml. of acetonitrile isadded with stirring 5.8 g. of l-ethyl imidazole. The reaction mixture isallowed to stand overnight at room temperature and then filtered. Thesolid 3 (2-perfluoro-n-propyl-4-amino-Smyrimidylmethyl)-l-ethylimidazolium chloride thus obtained is then' washed with acetone anddried to constant weight.

EXAMPLE 5 3- (Z-Perfluorobutyll-Amino-5-Pyrimidylmethyl) l-EthylImidazolium Bromide The procedure of Example 4 is followed and 14.6 g.of 2-perfluorobutyl-4-amino-5-pyrimidylmethyl bromide hydrobromidesuspended in ml. of acetonitrile is reacted with 9.6 g. of l-ethylimidazole to produce 3-(2-perfluorobutyl-4-amino-5-pyrimidylmethyl)-1-ethyl imidazoliurn bromide.

EXAMPLE 6 Di [3- (2-Perfluoroelhyl-4-Amino-5-Pyrimidylmethyl) -1- MethylImidazolium]-1,5-Naphthalene Disulfonate EXAMPLE 7 One gram of3-(2-perfiuoroethyl-4-amino-5-pyrimidylmethyl)-1-methyl imidazoliumbromide is dissolved in 4 m1. of concentrated hydrochloric acid. Theresulting solution is then diluted with 60 m1. 'of acetone and theprecipitate of 3 (2-perfiuor0ethyl-4amino-5-py1imidyl methyl)-1-methylimidazolium chloride which forms is recovered by filtration. This saltis then dissolved in about 2 ml. of concentrated hydrochloric acid andthe solution slowly diluted with about 40 ml. of acetone to precipitatethe 3 (2-perfiuoroethyl-4-amino-S-pyrimidylmethyD-l-methyl imidazoliumchloride which is then recovered by filtration and dried to constantweight.

EXAMPLE 8 3- [2-(3,3,3-Triflu0ropr0pyl') -4-Amin0-5-Pyrimidylmethyl] -1-M ethyl I mia'azolium Bromide H ydrobromide idylmethyl bromidedihydrobromide suspended in 50 ml. of acetonitrile is added 5.0; g. ofl-methyl imidazole. After allowing the mixture to stand for 20 hours atroom temperature the precipitate of 3-[2-(3,3,3-trifluoropropyl)4-amino-5-pyrimidylmethyl]-1-methy1 imidazolium bromide hydrobromidewhich forms is removed by filtration, washed with acetone and dried toconstant weight.

EXAMPLE 9 When the quaternary salts of Examples 2 3, 5 and 8 are treatedwith hydrochloric acid by the method of Example the correspondingchloride quaternary salts are obtained. i

EXAMPLE 1Q The 2 (3,3,3-trifluoropropyl)-4-amino-5-halomethyl and2-perfiuoroloweralkyl-4-amino-S-halomethyl pyrimidines employed inmaking the quaternary compounds of this invention may be prepared in thefollowing manner.

tained 2-perfluoroethyl-4-amino-S-bromomethyl pyrimidine hydrobromide.When 2-perfiuoro-n-propyll-amino- S-hydroxymethyl pyrimidine is employedas the starting material the end product isZ-perfluoro-n-propyl-4-amino- S-bromomethyl pyrimidine hydrobromide.When 2-(3, 3,3-trifluoropropyl)-4-amino-5-hydroxyrnethyl pyrimidine isutilizedas the starting compound there is obtained2-(3,3,3-trifiuoropropyl)-4-amino-5-bromomethyl pyrimidinedihydrobromide.

' 2- [Perfluoroloweraikyl or (3,3,3-trifluoroprop yl) ]-4-Amino-S-Hydroxymethyl Pyrimidine The2-trifluoromethyl-4-amino-S-hydroxymethyl pyrimidine employed in part Amay be prepared as described by Barone et al. in the [of Org Chem. 24,199 (1959). Barone et al. describe the preparation of the above compoundstarting with p erfluoroacetarnidine. When perfluoropr opionamidine,perfluorobutyramidine and 4,4,4- trifluorobutyramidine are utilized inthis process in place of perfluo-roacetamidine, there are obtainedrespectively 2-perfiuoroethyl-4-amino-S-hydroxymethyl pyrimidine, 2-perfluoro-n-propyl-4-amino-5-hydroxymethyl pyrimidine and 2'-(3,3,3-trifluoropropy1)-4-amino-5:hydroxymethyl pyrimidine.

The 'perfluoroalkylamidines referred to above may be prepared asdescribed in U.S. Patent No. 2,676,985, issued April 27, 1954. The4,4,4-trifluorobutyramidine also referred to above may be prepared inthe following manner:

' (1) A mixture of 100 g. of powdered 4,4,4-trifiuorobutyramide(prepared as described by Henne and Stewart, I. Am. Chem. Soc. 77, 1901(1955)) and 200, g. of phosphorus pentoxide is placed in a distillingflask fitted'with a condenser and receiver. The flask is slowly immersedin an oil bath which is maintained at a temperature of forms to thepresent invention is intended to be included within the scope of theclaims.

What is claimed is:

1. .An imidazolium compound selectedfrom the group consisting ofcompounds of the formula wherein R is a perfluoroloweralkyl radical, Ris selected from the group consisting of allyl and lower alkyl, X is anon-toxic anion, and b is a positive number having a value such that thenegative charge of the anion X is neutralized by b moles of cation andwherein R and X are as previously defined, and b and c are positivenumbers having values such that 12' moles of cation is neutralized by cmoles of anion X.

2. 3-(Z-perfluoroloweralkylt-amino-S-pyrimidyl-methyl)-1- al1ylimidazolium quaternary salt.

3. 3-(2-perfluoroloweralkyl-4-amino-5-pyrimidyl-methyl)-1-lower alkylimidazolium quaternary salt.

4. 3 [2 (3,3,3-trifluoropropyl)-4-amino5-pyrimidylmethylJ-l-lower alkylimidazolium quaternary salt.

5. 3 (2-perfluoroloweralkyl-4-amino-5-pyrimidylmethyl)-l-methylimidazolium quaternary salt.

6. 3 (2 perfluoroloweralkyl) -4--a.mino-5-pyrimidyltmethyl) -1-ethylimidazolium quaternary salt.

7. 3-(2-perfluoromethyl-4-amino-5-pyrimidylmethyl)-1- methyl imidazoliumhalide.

8. 3 (2-perfluoroethyl-4-amino-5-pyrimidylmethyl-lmethyl imidazoliumhalide.

9. 3 (2-perfiuoroethyl-4-amino-5-pyrimidylmethyl)-1- allyl imidazoliumhalide.

10. 3-('2-perfluoro-n-propyl-4-amino-5-pyrimidylmefnyl) -l-ethylimidazolium halide.

200230 C. As the reaction proceeds the 4,4,4-trifluorobutyronitrilewhich forms distills from the reaction mixture. After 5 hours of heatingvacuum is applied to the system to complete the distillation of thenitrile from V V the phosphoric acid residue. The crude nitrile obtainedis then distilled from 10 g. of phosphorus pentoxide at atmosphericpressure. 7 i

(2) To -a solution of 86 g. of 4,4,4-trifiuorobutyronitrile in 35.4 g.of absolute alcohol maintained at 0 C.

is added 28.1 g. of dry hydrogen chloride. The reaction mixture ismaintained at 0 C. for four days. 500 ml. of ether is then added and thereaction mixture cooled to about 30 C. The crystalline4,4,4-trifluorobutyrimido ethyl ester hydrochloride which forms is thenrecovered by filtration and washed well with ether.

(3) 100 g. of 4,4,4-trifluorobutyrimido ethyl ester hydrochloride isadded to a'stirred solution of 20 g. of ammonia in 200 ml. of ethanol.After 3 hours at room temperature the reaction mixture is filtered andthen concentratedin 'vacuo to a thick syrup. An equal volume of acetoneis then added and the precipitate of 4,4,4-trisodium .ethoxide inethanol to obtain the free base.

Any departure from the above description which con- 11. The processwhich comprises reacting an acid addition salt of a2-perfluoroloweralkyli-amino-S-hydroxymethyl pyrimidine ester of astrong acid with a l-lower alkyl imidazole to form a3-(2-perfluoroloweralkyl-4- amino S-pyrimidylmethyD-l-lower alkylimidazolium quaternary salt.

12. The process which comprises reacting an acid addition salt of a2-perfiuoroloweralkyl-4-arnino-S-hydroxymethyl pyrimidine estenofastrong acid with a l-allyl imidazole to form a3-(2-perfluoroloweralkyl-4-amino-5 F pyrirni dylmethyl) -1-allylimidazolium quaternary salt.

13. The process which comprises reacting an acid addition salt of a2-(3,3,3:trifiuoropropyl)-4-amino-5-hydroxymethyl pyrimidine ester of astrong acid with a 1- lower alkyl imidazole to form a3-[2-(3,3,3-trifluoropropyl)-4-amino-5-pyrimidylmethyl]-1-lower alkylimid- V azolium quaternary salt.

14. The process which comprises reacting an acid addition salt of a2-(3,3,3-trifluoropropyl)-4-amino-5-hy- 'droxymethyl pyrimidine ester ofa strong acid with a 1- allyl imidazole tovforrna,3-[2-(3,3,3-trifluoropropyl)-4- amino-5 pyn'midylmethyl] -l-allylimidazolium quaternary salt. f l

' References Cited in the fileof this patent V umrnnsrArns PATENTS2,146,083 Miller Feb. 7, 1939 2,279,421 Tisdale Apr. 14, 1942 2,350,265Williams et al May 30, 1944 2,587,262 Wilson et al .Feb. 28, 1952

1. AN IMIDAZOLIUM COMPOUND SELECTED FROM THE GROUP CONSISTING OFCOMPOUNDS OF THE FORMULA
 11. THE PROCESS WHICH COMPRISES REACTING ANACID ADDITION SALT OF A 2-PERFLUOROLOWERALKYL-4-AMINO-5-HYDROXYMETHYLPYRIMIDINE ESTER OF A STRONG ACID WITH A L-LOWER ALKYL IMIDAZOLE TO FORMA 3-(I-PERFLUOROLOWERALKYL-4AMINO - 5-PYRIMIDYLMETHYL)-L-LOWER ALKYLIMIDAZOLIUM QUANTERNARY SALT.